From Debt to Equity: Supporting Rapid International Scale

Cyber Guru is a Rome-based software company that offers an advanced security awareness training platform designed to help organizations reduce human risk – the leading cause of cybersecurity breaches.

Their comprehensive solution combines cognitive e-learning, real-life scenario-based videos, and contextualized phishing simulations that tailor training to each user's individual risk profile. Today, Cyber Guru is trusted by over 700 organizations across 90 countries, collectively serving more than one million active users worldwide. The company represents RAC's first investment in Italy's growing technology ecosystem.

Here's how they accelerated their international expansion and emerged as one of Southern Europe’s fastest-growing startups with the help of RAC's multi-stage growth capital.

Building from a Strong Base

When RAC first met the Cyber Guru team in early 2023, they had already established a noteworthy presence in Italy, with over 430 customers and 3.5M training lessons delivered. They had demonstrated the ability to secure major enterprise customers while maintaining capital efficiency and favorable unit economics.

The team was beginning to consider their Series B, but they saw an opportunity to continue their growth in Italy and further improve a couple key performance indicators before taking on a significant equity round and accelerating their international expansion strategy. After evaluating several growth capital providers, they chose to partner with RAC to bridge this period with non-dilutive funding, giving them runway to invest in growth.

Timing-wise, the company had just released version 2.0 of their platform, marking a significant leap forward in their technology that helped enable personalized security simulations. They were also taking their first steps into international markets through strategic partnerships.

We provided an initial growth loan to help accelerate this expansion. By structuring the investment as debt rather than equity, we helped give the team flexibility to continue investing in growth while further improving operations without triggering a valuation event before they felt ready.

Expanding Across Europe

Following RAC's initial investment, Cyber Guru's growth trajectory continued to accelerate. The team leveraged RAC's growth advisory resources, particularly the Riverside Revenue Acceleration System (RRAS), to help assess and finetune their sales and marketing strategy. They also worked with RAC operating partner Jonathan Temple, who helped them fill an opening for their first Vice President of International Sales.

The company expanded beyond its Italian base to establish a notable presence in strategic European markets like France and Spain. Their customer base grew from 430 to over 700 organizations, while their user base expanded to more than one million active participants across 90 countries.

The company's innovative approach to personalized security training resonated with enterprise customers looking to address the human element of cybersecurity risk. This success led to Cyber Guru’s recognition as one of Southern Europe's fastest-growing startups.

Leading a $25M Series B

In late 2024, the team felt ready to return to the equity markets. RAC led Cyber Guru's $25M Series B round, a progression from debt to equity financing that exemplifies our ability to support portfolio companies through multiple stages of growth with the right type of capital at the right time.

The Series B funding is primarily being used to help accelerate Cyber Guru's product roadmap, particularly enhancing their training capabilities to further optimize the learning experience. The investment will also fuel the company's continued expansion across Europe, with a focus on strategic markets where they've already established a presence.

As CEO Gianni Baroni noted, "Securing this investment from RAC and EduCapital, along with the continued support from Adara and P101, is an exciting step in our journey to scale internationally. Our mission is to improve organisations’ resistance to cyberattacks, by transforming user behaviour. With our proprietary Machine Learning model and the use of advanced adult learning methodologies, we’ve built a comprehensive security awareness training platform that is effective to manage and reduce human risk, and now we are poised to take this vision worldwide."

RAC's partnership with Cyber Guru demonstrates our commitment to supporting innovative business-to-business software companies with flexible growth capital solutions that can evolve alongside their needs. By providing the right capital at the right time – across both debt and equity – we've been able to help Cyber Guru on their journey to become a key player in cybersecurity awareness training.

Case study should not be relied upon for investment decision making and should not be considered an offer or solicitation of securities or investment services. For informational purposes only and intended for General Partners or Management teams considering partnering with The Riverside Company. Portfolio company selected based on non-performance criteria.